Methanesulfonyl chloride → HCID 59366517, compound

A mixture of 1.0 gram (0.003 mole) of 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)ethan-1-ol, 0.33 gram (0.0033 mole) of TEA and 0.37 gram (0.0032 mole) of methanesulfonyl chloride in 10 mL of methylene chloride was stirred at ambient temperature for two hours. The reaction mixture was diluted with 25 mL of methylene chloride and was washed first with 25 mL of water followed by 10 mL of a saturated aqueous sodium chloride solution. The organic phase was dried with magnesium sulfate, filtered and the filtrate concentrated under reduced pressure leaving an oil, which solidified upon standing. The solid was dissolved in 10 mL of DMSO to which 0.32 gram (0.005 mole) of sodium azide was added. The reaction mixture stirred at ambient temperature for about 18 hours at which time the reaction mixture was heated at 60° C. for one hour. The mixture was allowed to cool to ambient temperature, diluted with 25 mL of water and extracted with two 25 mL portions of ethyl acetate. The combined extracts were washed with 20 mL of an aqueous saturated sodium chloride solution, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure providing 0.86 gram of the subject compound as a foam. The NMR spectrum was consistent with the proposed structure.

1. washwas washed first with 25 mL of water
2. dry with materialThe organic phase was dried with magnesium sulfate
3. filtrationfiltered
4. concentrationthe filtrate concentrated under reduced pressure
5. customleaving an oil, which
6. additionwas added
7. stirringThe reaction mixture stirred at ambient temperature for about 18 hours at which time the reaction mixture
8. temperaturewas heated at 60° C. for one hour
9. temperatureto cool to ambient temperature
10. extractionextracted with two 25 mL portions of ethyl acetate
11. washThe combined extracts were washed with 20 mL of an aqueous saturated sodium chloride solution
12. dry with materialdried with magnesium sulfate
13. filtrationfiltered
14. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-ab383ec2687f436c899d2c955a09aed9

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017635B2